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Addition of N,N‐dibromosulfonamides to internal olefins: Synthesis of N‐sulfonylaziridines
Author(s) -
Foglia T. A.,
Haeberer E. T.,
Maerker G.
Publication year - 1970
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02541452
Subject(s) - stereoselectivity , selectivity , chemistry , base (topology) , ionic bonding , olefin fiber , medicinal chemistry , stereochemistry , organic chemistry , catalysis , mathematics , ion , mathematical analysis
The addition of N,N‐dibromobenzenesulfonamide (NNDBS) to internal acyclic olefins has been investigated. The major products formed were shown to be β‐bromosulfonamides. The reaction has been applied to pairs of cis‐trans olefins and has been found to proceed in a stereoselective fashion. To account for this observed selectivity an ionic mechanism has been proposed. The β‐bromosulfonamides prepared have been cyclized with base to N‐sulfonylaziridines. The configurations of the latter have been shown to be the same as those of the starting olefins.